


"She's not your sister anymore."

by liobi



Category: Critical Role (Web Series)
Genre: F/M, Implied Molly/Fjord, Kinky, POV Second Person, Sex
Language: English
Status: Completed
Published: 2018-01-28
Updated: 2018-01-28
Packaged: 2019-03-10 13:33:55
Rating: Mature
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,665
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/13502555
Author URL: https://archiveofourown.org/users/liobi/pseuds/liobi
Summary: You are the embodiment of chaos, of trickery. Now instead of turning every book in the store upside down, you're going to do that to someone's night.Or; Jester plays doctor with Caleb and it goes much better than expected





	"She's not your sister anymore."

“I’m not afraid of dicks.”

Caleb looks up at you, a little perturbed. When you continue to stare he cracks a nervous smile as he looks back to his book. “Good point.” He does shift away from you though. 

Nott, his little goblin friend, whispers to you. “He gets very focused, it’s best not to disturb him.” 

“Okay…” you sigh. 

Time passes, you nibble on a few cookies, but you feel the boredom setting in once again. Not even staring at the dirty wizard can fully alleviate it, as funny as the nervous glances he gives you are. He’s been reading that book for nearly a half hour now and you’re beginning to get curious once more. You wait for Caleb to become focused on the book again, and once he does you slowly lift yourself from the bench and begin to make your way around the table. 

A floorboard creaks under you, loud enough for Caleb’s attention to be broken. His eyes shoot up to meet yours and you give him a sheepish grin. He looks around the nearby area and spots a stool, immediately standing, grabbing it, and finding a new seat in a nearby corner. 

Caleb’s eyes meet yours, wearily this time. “Please, I am trying to focus.”

You attempt to peek over the corner, standing on your toes “I just want to-”

“Jester,” Fjord’s lazy drawl brings your attention back to the table. “Leave the poor man alone. If you’re bored, come over here, we’re tryin’ to figure out what to do next.”

Nott pulls her mask aside. “Should we go… look for the toad?”

-

Molly looks over at Caleb.

“Congratulations on single-handedly defeating the creature that killed several guards, I’m sure that you will be well rewarded and compensated.” Mollymauk gives a little bow towards Caleb before brushing some compost off his jacket.

“You are a very powerful wizard.” You say solemnly before breaking into a grin. 

Caleb nods. “You know, ain’t nothing” He stares back at you, his face serious. Then he breaks into a fit of wet coughs as the last bit of blood expels itself from his lungs. He then makes a noise that’s somewhere between a groan and a scream, and you can’t help but laugh. 

As you stare at this beat up man, you feel a strange urge, much like the one you felt in the bookstore. The urge to create chaos, to have fun, to do something unexpected and turn everything upside down. As he slowly pulls himself to his feet, you feel something spark inside. 

A warm wind brushes against you. The Traveller has been your constant companion for as long as you remember. You’re not sure if he can read your thoughts but he knows you well enough, and it seems he approves. As you look closer, you become more sure of yourself. Under all of that dirt, and whatever else may be mixed it, Caleb may not be half bad looking. 

-

You all make your way back to the Nestled Nook Inn after dropping Toya at the circus without issue. None of you are tired enough to go to sleep yet, it’s only two in the morning after all, and you slept in much later than you had anticipated earlier in the day. Add in a dash of adrenaline and, with the exception of Caleb, everyone heads down to the main hall to get some food and drink. 

“I’m going to take it easy, maybe turn in a little early.” He says as the rest of you begin to make your way downstairs. He grins a little as he pulls out what looks to be an old sketchbook, “Besides, I still have one more book to read.”

“Should I stay with you?” Nott looks at him, worried. “I can. I could even sing you to sleep if you wanted.”

Caleb winces. “Not tonight. You go, have fun, fill your new flask.” He pats her head and she leans into it a little. “I will be fine.”

You stare a little longer at the door as it closes behind him. “Yo, Jester!” Beau calls, halfway down the stairs. “You coming or what? It’s time to celebrate, man!” You flash a smile as you agree and follow, skipping down the stairs the whole time. 

Molly buys everyone a round, and you order a few pastries. The barmaid looks at you a little strangely but agrees anyway. It’s not long before Fjord and Molly are admiring each other’s swords and swapping stories of the circus and the sea, and Nott and Beau, already well into their cups, begin singing some offkey rendition of a local folk song. 

After the barmaid comes back with your pastries, and a quick glance around to see that no one’s really paying you much mind, you dart up the stairs towards Caleb’s room. 

Once you get there, you knock. “Caleb? Hello, it is Jester. I am here to check on your wounds.” Nothing. “I brought pastries” You hear a groan of pain from inside and slow, labored footsteps towards the door. As it opens, you find yourself in front of a shocking sight. “All of the dirt is gone!”

Caleb stands in the doorway, shirt off, towel draped around his neck, and most of his torso covered in bandages. “It would be very bad if any of these were to get infected.” He shrugs. “So yes, I cleaned. The dirt is no more.” 

Now that it’s gone, you can see that you were not wrong about his appearance. Under the filth hid a strong jawline and high cheekbones. His face is a bit gaunt, whether from disposition or hardship, and his body while lean is well defined from his time on the road. You stare at him as he begins to shift, uncomfortable. “Soooo, can I come in?”

Caleb shifts to one side slightly and you seize the opportunity, darting into the room. He looks over at you, surprised at your speed. “Sure, I guess.” He shrugs, walking in after you as the door swings closed. “How is it downstairs.”

“You know, Molly and Fjord are admiring each other’s swords, they are talking about the circus and seamen.” That gets a chuckle out of Caleb. “Beau is celebrating a lot, with booze. Nott is also celebrating a lot. You know you should laugh more, less people would call you a sourpuss if you did.”

“Oh? Are people calling me a sourpuss now?”

“Well, less people would if you laughed. Like, at all.” You’re noticing now, when he’s at ease a small smile creeps onto his face. It’s a nice smile. “You should have more fun! You should celebrate too!”

“But I am celebrating.” He nods towards a pint you now see on the bedside table next to the candle and the sketchbook. “It’s just a different way right now. We fought and defeated a demon, we will be clearing our names, we are like heroes out of the stories, we’ve even found new friends. There is a lot to celebrate. It is also a lot to process.” 

An awkward silence starts blooming between you two but before it can take root you put the pastry on the table and point at the bed. “Sit, let me check your wounds.” He complies, draping the towel on the back of the chair. 

As you begin examining him, Caleb clears his throat. “So, how did you become a cleric?”

You shrug. “It’s not that interesting of a story. How did you become a wizard?”

“That is also not a very interesting story.”

Your fingers slowly trace down his torso. “Does it hurt if I push here?”

He grunts. “Yes.”

“Here?”

“Oof. Also yes.” He looks down at you. “No offense, but are you sure you know what you are doing?”

“No, I am just here poking you to see what kind of funny faces you make. Of course I know what I am doing, I am a trained healer!” Caleb looks to the side, embarrassed. “Jeez.”

“I’m sorry.” He sighs, his eyes coming back to your own. “I just don’t know you that well yet. Meeting new people can be… difficult sometimes.” 

You nod. “Hello, it is nice to meet you. I’m Jester.”

“Hello, I’m Caleb.” he gives that small smile again. “It is nice to meet you.”

“See? Now we have met each other.” Your prods soften as your fingers begin tracing along his bandages. “Does this hurt?”

“No.”

Your fingers begin tracing below the bandages, trailing towards his abdomen. “How about now.”

Caleb shivers despite himself. “Not exactly. Jester, what exactly are you-” he cuts himself off with a small gasp as your fingers quickly trace the line where his trousers meet his waist. 

“I am examining you, what does it look like?” he’s about to say something but he cuts himself off again as your light touches become more for a brief second, your nails digging into his unmarked skin.

“This does not feel professional anymore.” He is trying to catch his breath and his cheeks turn red. You can feel your own face tingeing blue. But when you glance at him, his quick small breaths, you get that feeling again. Much like turning a book upside down in a shop without anyone noticing, this is satisfying in a way that resonates deep inside you. 

The bed creaks as you put your knees on either side of him and pull yourself forward. “Well for your information, I am being very professional and very thorough.” Caleb’s lips part slightly as his breath escapes him. “Who is the trained healer again?”

“That… would be you.” he begins to trail off as you pull your face closer to his. 

“That’s right. Doctor’s orders.” And you press your mouth against his. Caleb’s thin lips are surprisingly soft against your own. You close your eyes, enjoying the moment, your mouth opening against his. And then your teeth find his bottom lip.

“Ach!” he breaks away with a start, feeling his lip with his tongue. He looks at you curiously. 

“Did that hurt?”

“Of course it hurt, it was my lip”

“Oh no!” You cover your mouth in mock horror. “This may be more serious than I thought! I will have to check everything.” You hand grasps a handful of his hair at the back of his head and you pull his mouth to yours yet again. This kiss is a little more intense. Somewhere between violent and desperate, you both shift so you’re on the bed completely and no longer sitting over the side, the kiss breaks again as both of you come for air. 

Your hand stays firmly clasped in Caleb’s hair as your other hand traces up his back with your nails and then down his torso with your fingertips. “Jester.” He gasps your name quietly, looking up at you.

You nod. “Do not worry about me. I am stronger than you.” To prove it you pull his head back exposing his neck and slowly begin to leave kisses and small bites down towards his collarbones. The small, choked noises coming out of his mouth are like music to your ears. 

His hands shakily begin to unbutton your shirt, though the further down he gets the more his confidence grows. It is not long before the shirt has been discarded and your band has been pulled off and discarded onto the floor. His teeth find your breast and you gasp, digging your fingernails into his shoulder and pulling his hair back tightly. He grunts in pain.

“Careful!”

“Oh stop being such a baby. I am a healer, I know exactly what I’m doing.” You look him in the eye, and after a moment he nods. You bite into his collarbone and he grunts again, his nails digging into your skin. After you let go, you slowly trace the bite mark with your tongue. 

Caleb’s hands begin to wander lower, and eventually they find their way under your skirt. You’re excited enough that there’s no issues with friction, and he begins to get to work, slowly rubbing and circling your clit. He’s good with his fingers, though that shouldn't surprise you considering the complex hand motions that any caster would have to perform for their craft. You pull his hair tighter, gasping a little, as shivers travel down your thighs and up your spine.

He sees the way you react and he becomes more focused, repeating what makes you moan the loudest while slowly exploring the rest of you with his free hand. You shiver again as he scratches down your back before his hand finds your ass and grabs it firmly. His fingers focus more and more until you gasp, your whole body shivering. 

He stops. “Are you-”

You yank his hair back. “You are not done yet, Mr. wizard. Inside. Now.” 

Caleb’s eyebrows raise but he complies, curling his fingers inwards. One at first, then two. You sigh as the after effects of your orgasm have made you sensitive. Not to be outdone, your hand travels down his chest and into his trousers. Your hand finds what you were looking for, and you grasp it softly. Caleb lets out a soft moan and you grin, your fingers slowly tracing up and down. 

“Well Mr. wizard? How are you doing?”

“You are the healer. Shouldn’t you know what is going on with my body.” He smirks back at you before he shudders as you wrap your hand around him and slowly continue your up and down motions. 

You stay like that for a little while, enjoying the feeling of his fingers back and forth inside of you, the way his mouth opens and closes as he squirms and gasps under your grasp. “Caleb.”

He moans but looks up at you. 

“Take off your trousers.” As he follows your instructions, you discard your own skirts. He looks at you, waiting for something. “Well? Lean back where you were, dummy!” As he does, your eyes take him in his entirety. There's not much meat on his bones, but what’s there is well defined. His dick isn’t half bad either.

You dig your nails into his thighs as you begin to lower your head between his legs. He groans, but his eyes catch yours and you stop.

“Jester, are you sure?”

“I told you already, silly. I’m not afraid of dicks.”

He can’t keep back the sound of his voice as you begin to leave a trail of kisses down his stomach, and then lower still. He shivers when you gently slide your tongue across the tip, and when you take him inside your mouth his breath hitches and he begins to moan loudly. 

Then, you drag your teeth against him. He jumps and looks at you alarmed. “What exactly are you doing?”

“What, are you not having fun?”

“I am but-”

He moans as you plant light kisses where you had your teeth, followed by your tongue trailing over it. “I mean if you want me to stop or you don’t trust me, I would completely understand.”

“No I- you know what?” he swallows. You can see he’s nervous, but the blush in his cheeks betrays his excitement as well. “I trust you.”

You smile and bring Caleb back in with renewed enthusiasm. He writhes against you, and when you look to the side you see the healer’s kit Beau gifted you. You get an idea. 

“You cleaned everywhere, right? Because it would be really stupid and gross if you washed but didn’t do that.”

He looks down at you, dazed and confused. “Yes. I’m… what?”

You smirk at him and scoot to the edge of the bed. You manage to snag the healer’s kit and pull it up next to you. “Hang on i just need to find something really quick and oh there it is!” You pull out a small jar of grease. Normally it would be used to treat burns in a pinch, but you have some other, more fun ideas for it. You quickly coat two of your fingers with it and press them gently between Caleb’s legs. “May I?”

He meets your eyes and hesitates for a second, but then nods. You smile, grasping his thigh as you gently push against him and after a little while your fingers slowly slide inside. His breath hitches a little as you slowly begin to curl your fingers inside of him. “Are you good?”

Caleb nods. “Yeah. Yeah I’m good. Just, not quite used to… this.”

You begin to leave kisses down his thigh. “Don’t worry. I won’t break you” A look of worry flashes on his face before you take him in your mouth again. If his moans were loud before, he’s practically yelling now. As you pump your fingers inside of him he shakes under you. His hands grasp at the bed, the wall, the headboard, until at last they travel downwards and find your head where he grabs you by the hair.

“Oh, gods-harder, please”

You’re happy to comply, putting more strength into your thrusts and judging his reactions to make sure you’re hitting the right spots. 

“Oh fuck. Fuck… Jester, I’m-”

You immediately pull out of him and bring your mouth to meet his. It’s furious and warm and when you break the kiss he gasps for air like he was drowning. “Not yet, mister. There are plenty of fun things left to do, you can’t stop here.” His gasps slowly turn into labored breaths. He nods.

You look around the room and notice that the washing basin is on the other side. You look down at your grease covered fingers and sigh. “Hang on, I just have to wash this off. I don’t want skinky doody on anything it is not supposed to be on.”

Caleb grabs your arm. “Hang on” he mutters something and waves his fingers and suddenly the grease is gone, and you feel as if your hands have been cleaned. “Prestidigitation is a very useful cantrip.”

“Works for me!” You climb on top of him once more. Using your hand you begin to guide him in-

“Wait, hang on!” You stop and look at Caleb. “What about protection, we-”

You hold up your wrist and show him your bracelet. From it hangs a charm that catches the nearby candlelight. “Protection charm. Protection from pregnancy, disease, blah blah blah.”

“Well, that’s that then” 

You resume guiding him inside and once that’s done, you sink down against him. You both shudder and his breathing grows faster. You give it some time to adjust to him inside of you and then you begin to rock against him. 

Nearly every time you come down he gasps or moans, and you can’t help but think how fun it is to be the cause of all these faces he’s making. Your hand finds the back of his head again, and his wrap around your hips as you pick up the tempo. He’s moaning near constantly now, and you move your free hand between your legs and begin to help yourself out. 

His gasps and moans become more and more frequent until they are just one continuous song against your ears. You keep yourself just at the edge with your hand until he’s gasping, calling your name, begging you. You pull his hair back and his hand reaches out, finding its grip on your horn. 

Your fingers gently circle again and again until you can’t hold onto the edge any longer and the orgasm rocks your whole body. And as you shudder and squeeze around Caleb, he loses it himself and screams your name, grasping your horn tight until he falls back into the bed, exhausted. 

Exhausted, you pull yourself off of him and flop down beside him. You both lay there, catching your breath until he breaks the silence. 

“That was… wow.”

You giggle. “I’m glad you enjoyed yourself.” 

He stares at the ceiling for a bit longer before he turns to you. “So… what brought this on?”

You purse your lips and consider for a little while. “You know, I just thought it would be fun to mess with you for a little while.”

He looks at you, as if he doesn’t know what to say. And then it starts. First a smirk, then a chuckle, then full on laughter as he drapes his arms around you. “Yes that… that was very fun indeed.”

-

The next morning you hear a knock at the door. Your eyes open and you see the still naked body of Caleb next to you. The knock goes again. 

“Hold on a minute I’m naked!”

“Oh! I’m sorry. Uh. I can come back another time.” Nott’s voice rings through the door. “But if you could tell Caleb that breakfast is ready that would be great.”

As the smell of bacon, sausage, eggs, and many other things wafts up into Caleb’s room as you rouse yourselves and get ready for the day. Somehow, you manage to stumble out of the room at the same time as everyone else. Beau stumbles out of your room complaining about how much her head hurts, and Molly and Fjord seem to be having an argument as they step out of their room. 

You do notice that Molly has come out of the room with barely any clothes on, just trousers and the shirt he is currently buttoning up. You also notice that both he and Fjord are each sporting some very interesting bite marks on their necks, and Molly many other places as he finishes buttoning his shirt. 

“I’m just saying, I never expected you to be verse.” Molly calls after Fjord as he tries to put distance between them. “Oh, and thank you for showing me those cloisters of seamen first hand!”

“I’m walking away!” Fjord calls as he disappears down the stairs. 

You giggle and follow after, skipping down the stairs. It’s gonna be a good day.

**Author's Note:**

> Yeah as soon as Marisha said "She's not your sister anymore" I knew that I was probably going to write this fic. Whoops


End file.
